My Uber driver, Stephen, zoomed out of downtown Milwaukee like a bat out of hell.

“You don’t mind the windows open, do you? It’s too nice of a day to have them closed.”

Not about to deny him fresh 60-degree air, I snuggled deeper into my fleece jacket and settled in for the ride. I decided not to mention that I had just come from 80-degree weather in D.C.

Our destination: Bay View, a historic and popular neighborhood a few miles south of downtown.

Did I know what to expect when I arrived? No. To be honest, I’m clueless when it comes to Milwaukee. Despite growing up the next state over (Minnesota) and visiting Chicago multiple times each year, I’ve never made it to Wisconsin’s most populous city. I could say it’s been “on my list,” but the reality is it hasn’t been very high.

Turns out it should have been.

In town for a conference, a local directed me to Bay View to check out “a James Beard-quality chef who will never win the award.” Not one to pass up a memorable meal recommendation, I was in.

Stephen exited I-94 and pulled onto South Kinnickinnic Avenue, what I assumed to be Bay View’s main drag.

Bay View neighborhood, Milwaukee, Wisconsin

South Kinnickinnic Avenue

The neighborhood had an air of subdued resurgence. Aged brown brick buildings housing offbeat shops and restaurants with vintage-looking signs selling real vintage goods. Dudes with beards. Skateboards. Leather. Signs displaying “The Alchemist” and “Hi-Fi Cafe.” A mix of old and new, with the new carefully designed to fit in with the surroundings so as to not lose “that authentic feel.”

Bay View neighborhood, Milwaukee, Wisconsin

I walked up and down South Kinnickinnic, taking in Bay View’s unique atmosphere. (The street name made me think of Kenickie from Grease. Anyone with me?)

Bay View neighborhood, Milwaukee, Wisconsin

Rushmor Records

I came across Shape Up Shoppe – what I assumed to be an ice cream joint – toward the end of the commercial district, blaring “Backstreet’s Back” from its open door. Intrigued, I stepped inside to find a gym with aged blue equipment and not a soul in sight.

I wandered for a few more minutes before circling back to my destination: The Vanguard, an inconspicuous upscale dive (oxymoron?) wedged between the Shape Up Shoppe and a series of vintage stores and bakeries.

The Vanguard in Milwaukee, Wisconsin

The Vanguard

It was 7:00 and The Vanguard was hopping. The amount of people inside the bars and restaurants on South Kinnickinnic sharply contrasted with the empty roads and sidewalks outside. So this is where the people are.

I settled in at the bar – the only way to experience in a place like this – and took in my surroundings. Burly locals to my right playing Rock-Paper-Scissors for shots of Four Roses. A casual couple to my left unwinding after work. An old WWE fight on TV and classic hits streaming above the dozens of conversations that filled the space with energy.

The Vanguard, Bay View, Milwaukee, Wisconsin

I was instructed to order two things at the restaurant: a cocktail called the Settlers Punch and one of The Vanguard’s famous styled sausages.

The story of the Settlers Punch goes like this: The local who referred me to the bar is a friend of the owner and a regular at The Vanguard. One day, she and her husband went into the bar and asked for a cocktail that was made with “anything but gin.” The bartender agreed to whip something up that she would enjoy. She sipped the resulting drink – a bright, citrusy, spiced concoction – and loved it.

I’m sure you’ve already guessed what was in it. Yep – gin. It became a cocktail menu staple from that moment on, and I must say, being no ginthusiast myself, I quite liked it.

The Settlers Punch at The Vanguard in Milwaukee

The Settlers Punch

I ordered the Gypsy Mitch – an artisan sausage – for dinner, with a side of cheese curds. I figured fried cheese could act as a suitable french fry substitute for the evening. When in Wisconsin.

I pondered my strange relationship with sausage as I waited for them to prepare my food. I enjoy sausage in a meal from time to time, but on most occasions the thought of it makes me mildly nauseous. I’m either on one end of the spectrum or the other, and never in the middle.

On this night, I prepared myself to go in, give their styled sausages a try, check the “I-had-sausage-in-Milwaukee” box, and never think about it again.

My food came about 15 minutes later. Go time.

I took my first bite of the Gypsy Mitch. Set it down. And scribbled in my notes.

This sausage is a holy-sh*t moment.

Maybe it was the slight sweetness from the Dr. Pepper it was cooked with. Or perhaps the cotija cheese, arugula and lime aioli on the bun balanced it out just right. Whatever it was, the Gypsy Mitch had depth and balance that made me rethink my entire idea of sausage’s place in the food hierarchy. Could sausage actually be gourmet? It certainly is at The Vanguard.

The Gypsy Mitch and cheese curds at The Vanguard in Milwaukee

The Gypsy Mitch and cheese curds

The cheese curds had a lower bar to pass. Cheese happens to be my favorite food group, so the addition of a fried casing only made me love it more. If my arteries could bear it, I would replace french fries with cheese curds at every meal.

I ate as much as I could, but the meal’s richness eventually wore me down. Cheese curds were an aggressive option to pair with a sizable sausage dinner. I offered some cheese curds to my new friends on the right, who were still playing Rock-Paper-Scissors for shots (this time with the bartender).

I spent the rest of the evening befriending the lively fellows to my right, chatting intermittently with the bartender, Nick, and even meeting The Vanguard’s owner, Jim, who happened to be there for the beer event that my burly barmates were hosting.

After trading drinks, stories, sarcastic jokes, and even Snapchat handles long into the night, I realized it was time to head home. Three hours after arriving, I felt like a local and had been embraced like one.

Milwaukee, you may not have been high on my list before, but you are now.

If You Visit The Vanguard

  • Website
  • Known for: Artisan sausages, bourbon selection
  • Address: 2659 S Kinnickinnic Ave, Milwaukee, WI 53207
  • Attire: Casual
  • Price: $5-8 for a sausage, $8 cocktails
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